Category: indolines-derivatives

Related Products of 20780-77-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 20780-77-2 name is 6-Iodoindoline-2,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Method IAccording to this method Examples 1-14 and 22-24 were prepared. The indirubin derivatives are prepared according to Russel G. A., Kaupp G. (1969), J. Am. Chem. Soc., 91, pages 3851-3859. ; Example 1 6-iodo-indirubinYield: 68%, fine deep-purple powderCHN-analysis: C16H9IN2O2 (MW: 388.16 g/mol) calc.: 49.5%; C, 2.3%; H, 7.2%; N. found: 49.3%; C, 2.1%; H, 7.1%; N.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodoindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Faustus Forschungs Cie. Translational Cancer Research GmbH; US6987092; (2006); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 5-Methoxyindolin-2-one

General procedure: To a solution of 4-(4-(hydrazinecarbonyl)-5-phenyl-1H-pyrazol-1-yl)benzenesulfonamide (10) (10 mmol, 0.36 g) in 20 mL ethanol, 10 mmol of 5-(un)substituted isatin or N-benzyl isatin was added followed by catalytic amount of acetic acid (0.5 mL). The reaction mixture was refluxed for 1 h. The formed precipitate, in case of 11a-e, was filtered, washed with hot ethanol and recrystallizedf rom DMF/ EtOH to give the targeted compounds 11a-e. Concerning compound 11f, the precipitate formed after cooling was filtered and recrystallized from DMF/ EtOH. 4.1.5.4 4-(4-(2-(5-Methoxy-2-oxoindolin-3-ylidene)hydrazine-1-carbonyl)-5-phenyl-1H-pyrazol-1-yl)benzenesulfonamide (11d) Orange powder, 81% yield; mp > 300 C. IR (KBr) numax/cm-13414-3190 (NH2, NH), 1722-1690 (C=O), 1512 (C=N), 1322, 1156 (SO2). 1H NMR (DMSO-d6, 300 MHz) delta 3.77 (s, 3H, OCH3), 6.81 (dd, 1H, J = 11.4, 8.6 Hz, H-7 of isatin), 6.91-7.08 (m, 1H, Ar-H), 7.30-7.43 (m, 6H, Ar-H), 7.45 (s, 2H, SO2NH2, D2O exchangeable), 7.80 (d, 2H, J = 8.7 Hz, Ar-H), 8.34, 8.49 (2s, 1H, H-3 of pyrazole), 10.55, 11.02 (2s, 1H, NH isatin, D2O exchangeable), 11.31, 13.12 (2s, 1H, NH hydrazone, D2O exchangeable). 13C NMR (DMSO-d6, 75 MHz) delta 55.58, 105.73, 110.91, 111.91, 112.39, 115.65, 118.23, 120.46, 125.74, 126.50, 128.29, 129.23, 130.23, 135.90, 137.35, 141.14, 142.19, 143.31, 154.45, 155.32, 162.60, 164.74. MS m/z [%] 516 [M+, 7.62], 326 [100]. Anal. Calcd for C25H20N6O5S (516.53): C, 58.13; H, 3.90; N, 16.27; S, 6.21. Found: C, 58.30; H, 3.96; N, 16.38; S, 6.32.

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ibrahim, Hany S.; Abou-Seri, Sahar M.; Tanc, Muhammet; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 583 – 593;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 17630-75-0 as follows. Quality Control of 5-Chloro-2-oxindole

A mixture of 5-chlorooxindole (6.98 g, 41.6 mmol), 3,5-dimethyl-1H-pyrrole-2-carboxaldehyde (5.12 g, 41.6 mmol) and piperidine (410 muL, 4.16 mmol) in 200 mL of EtOH was heated at reflux for 8 h. The reaction mixture was cooled to room temperature and filtered to give the title compound (4.50 g, 40%) as a red/orange solid.

According to the analysis of related databases, 17630-75-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US2004/102509; (2004); A1;,
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Application of 104618-32-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 4 3-Amino-6-bromo-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-bromophenylhydrazine hydrochloride (4.0 g, 18.1 mmol) with 4-phthalimido-cyclohexanone (4.39 g, 18.1 mmol) in refluxing n-butanol for 20 min, followed by cooling, filtration, and evaporation of the filtrate to dryness yielded 3-phthalimido-6-bromo-1,2,3,4-tetrahydrocarbazole as an orange solid (7.45 g).

The synthetic route of 2-(4-Oxocyclohexyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
Indoline – Wikipedia,
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Related Products of 71294-03-6, These common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 53Preparation of 5-f(2-(riS.2SV2-ri-(5-chloropyrimidin-2-vnpiperidin-4- yllcYclopropyUethy?aminol-T-fluoro- 1 ,3-dihvdro-2H-indol-2-oneStep 1: 7-fluoro-5-tauiitro-L3-dihvdro-2H-indol-2-one7-fluoro-1,3-dihydro-2H-indol-2-one (8.Og, 52.9 mmol) was slurried in H2SO4 (cone, 86 ml) and the mixture cooled to -45 C. A solution of fuming nitric acid (>90%, 3.34 g, 52.9 mmol) in H2SO4 (20 ml) was added drop wise, while maintaining the temperature at -45 C throughout the addition. The mixture was allowed to slowly warm to RT and stirred overnight. The mixture was poured into stirred ice-cold water (1500 ml). A white precipitate resulted, and the slurry was aged at 0 C for 1 hour. The solid was collected by filtration, triturated with cold water (2x), and dissolved into EtOAc (1 L). TWs solution was washed with basic brine (containing sodium bicarbonate), dried over Na2SO4, filtered, and the volatiles removed in vacuum to give the titled compound.

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
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Related Products of 20870-79-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 20870-79-5 as follows.

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

According to the analysis of related databases, 20870-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromo-1-methylindoline-2,3-dione

In a 50 mL reaction flask,Triethylamine (40 mg, 0.4 mmol)Was added to a solution of 1-methyl-5-bromoisatin (240 mg, 1.0 mmol)1-cyanoacetylguardane azulene (344 mg, 1.3 mmol)And malononitrile (86 mg, 1.3 mmol)In acetonitrile (30 mL)Heated to reflux for 7 hours (monitored by silica gel chromatography (TLC)). After completion of the reaction,The reaction mixture was concentrated under reduced pressure and recrystallized from acetic acid to give a blue solid in 80% yield.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2058-72-2.

Reference:
Patent; Bohai University; Wang Daolin; Zhang Weinan; Xing Jinjuan; (14 pag.)CN106220641; (2016); A;,
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Reference of 41910-64-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of an HCl salt of Intermediate JB-2 (35 mg, 0.11 mmol) in DCE (0.50 mL) was slowly added to a stirred solution of sulfurisocyanatidic chloride (0.014 mL, 0.16 mmol) in DCE (0.25 mL) at 0C and the reaction mixture was allowed to stir at 0C for 1 h. The reaction mixture was treated with a solution of TEA (0.049 mL, 0.35 mmol) in DCE (0.25 mL), stirred at 0C for 5 minutes and then added to a solution of 4- chloroindoline (33.5 mg, 0.218 mmol) in DCE (0.25 mL). The reaction was sealed, shaken at rt for 2h, concentrated and then purified by preparative HPLC to yield the title compound. LC-MS retention time = 2.70 min; m/z = 543.2 [M+H]+. (Column: Waters BEH C18, 2.0 x 50 mm, 1.7-muiotaeta particles. Solvent A = 95% Water : 5% MeOH : 10 mM NH4OAc. Solvent B = 5% Water : 95% MeOH : 10 mM NH4OAc. Flow Rate = 0.5 mL/min. Start % B = 0. Final % B = 100. Gradient Time = 3 minutes, then a 0.5-minute hold at 100% B. Wavelength = 220). 1H NMR (500 MHz, DMSO-d6) delta 7.30 – 7.25 (m, 1H), 7.16 – 7.07 (m, 5H), 7.02 – 6.98 (m, 2H), 6.96 – 6.92 (m, 2H), 6.71 (d, J=7.3 Hz, 2H), 6.59 (d, J=8.4 Hz, 1H), 4.31 – 4.25 (m, 1H), 4.20 – 4.13 (m, 1H), 4.12 – 4.06 (m, 1H), 3.79 (s, 3H), 3.07 (s, 3H), 3.07 – 3.01 (m, 2H), 2.74 – 2.69 (m, 1H), 2.44 (dd, J=13.6, 7.7 Hz, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Chloroindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 19727-83-4, name is 6-Nitroindoline, A new synthetic method of this compound is introduced below., Recommanded Product: 19727-83-4

To a solution of 6-nitroindoline (1.00 g, 6.09 mmol) and pyridine (1.48 mL, 18.27 mmol) in DCM (3 mL) was added a solution of t- butylsulfinyl chloride (0.751 mL, 6.09 mmol) at 0 C under Argon. The mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with EtOAc (50 mL) and washed with HC1 (1 M aq. solution, 1 x 50 mL), water (1 x 50 mL), and brine (1 x 50 mL). The organic layer was dried (Na2S04) and concentrated under reduced pressure. The resulting residue was triturated using EtOAc/hexanes to provide the title compound as a dark yellow solid (1.252 g, 77%). Mp: 108 C (dec). NMR (400 MHz, CDCb) delta: 7.82 (dd, / = 8.1, 2.1 Hz, 1H), 7.67 (d, / = 2.1 Hz, 1H), 7.25 (d, / = 8.1 Hz, 1H), 4.36 (td, / = 10.5, 6.8 Hz, 1H), 3.60 (td, / = 10.5, 6.8 Hz, 1H), 3.30 (dddd, / = 17.3, 10.5, 6.8, 0.8 Hz, 1H), 3.17 (dddd, / = 17.3, 10.5, 6.8, 0.8 Hz, 1H), 1.34 (s, 9H). HPLC-MS (ESI+): m/z 559.3 [70%, (2M+Na)+], 291.2 [100%, (M+H)+].

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6326-79-0,Some common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred solution of sodium hydroxide (0.48 g, 12.0 mmol) in water (8 ml) was added 6-bromoisatin (2.5 g, 11.0 mmol). The reaction mixture was gently heated until it became dark red. This dark-red solution was cooled to 0 C and mixed with a solution of sodium nitrite (0.76 g, 11 mmol) in water (3 ml) at 0 C. The combined solution was then added to a rapidly stirred solution of sulphuric acid (1.1 ml, 22.0 mmol) in water (42 ml) via dropping funnel at 0 C. The rate of addition was maintained such that the temperature of reaction mixture should not rise above 5 C. After completion of addition, the brownish- yellow solution was stirred for 15 minutes. Then a cold solution of stannous chloride dihydrate (6 g, 26.5 mmol) in concentrated hydrochloric acid (10 ml) was added from a dropping funnel to the stirred solution of the diazo-compound. The mixture was stirred for another 1 hour after the addition was complete. The crude product, a yellow to brown paste, was collected on a Buckner funnel (1.75 g, 65%) and used for the subsequent step directly without further purification. LCMS: m/z = 239.16 [M-l], 241.20 [M+l].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisatin, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMCEUTICALS, INC.; WILSON, Jonathan, E.; LEVELL, Julian, R.; (152 pag.)WO2019/161157; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem